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[ CAS No. 7748-36-9 ] {[proInfo.proName]}

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Product Details of [ 7748-36-9 ]

CAS No. :7748-36-9 MDL No. :MFCD09056790
Formula : C3H6O2 Boiling Point : -
Linear Structure Formula :- InChI Key :QMLWSAXEQSBAAQ-UHFFFAOYSA-N
M.W : 74.08 Pubchem ID :9942117
Synonyms :

Calculated chemistry of [ 7748-36-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 5
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 16.67
TPSA : 29.46 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.99
Log Po/w (XLOGP3) : -0.77
Log Po/w (WLOGP) : -0.62
Log Po/w (MLOGP) : -1.03
Log Po/w (SILICOS-IT) : 0.64
Consensus Log Po/w : -0.16

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.19
Solubility : 114.0 mg/ml ; 1.53 mol/l
Class : Highly soluble
Log S (Ali) : 0.63
Solubility : 315.0 mg/ml ; 4.26 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.49
Solubility : 228.0 mg/ml ; 3.08 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 7748-36-9 ]

Signal Word:Danger Class:N/A
Precautionary Statements:P261-P264-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H318-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7748-36-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 7748-36-9 ]
  • Downstream synthetic route of [ 7748-36-9 ]

[ 7748-36-9 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 7748-36-9 ]
  • [ 6704-31-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3227 - 3246
[2] Patent: WO2011/29043, 2011, A1, . Location in patent: Page/Page column 120
[3] Tetrahedron Letters, 2013, vol. 54, # 44, p. 5849 - 5852
[4] ACS Catalysis, 2013, vol. 3, # 11, p. 2612 - 2616
  • 2
  • [ 95257-22-0 ]
  • [ 7748-36-9 ]
YieldReaction ConditionsOperation in experiment
95.84% With palladium 10% on activated carbon; hydrogen In methanol at 40℃; for 24 h; Autoclave 1-5 ( 59 g · 98 , 600 · 41mmol) and 10percent palladium on carbon in methanol (1 (λ OOg) was added 1000ml of hydrogenOf the autoclave , the reaction temperature at 40 ° , 10atm , the reaction 24h, the hydrogenation was completed, the palladium carbon by filtration , the solvent was concentrated under reduced pressure.Distillation colorless liquid product 142 · 63g, yield 95. 84percent;
Reference: [1] Patent: CN103554064, 2016, B, . Location in patent: Paragraph 0031; 0032; 0041; 0042
  • 3
  • [ 85328-36-5 ]
  • [ 7748-36-9 ]
YieldReaction ConditionsOperation in experiment
95% With toluene-4-sulfonic acid In methanol at 15 - 18℃; for 0.75 h; A solution of Part C compound (15 g, 103 mmol) in MeOH (5.26 mL, 125 mmol) was cooled to 15-18° C., and p-TsOH (100 mg, 0.581 mmol) was added with stirring. The reaction mixture was stirred for 45 min, after which NaHCO3 (50 mg, 0.595 mmol) was added. Distillation at 35-40° C. (0.1 mmHg) gave crude Part D compound (7.0 g, 95percent) as a clear oil.
Reference: [1] Patent: US2008/9465, 2008, A1, . Location in patent: Page/Page column 82
[2] Journal of Organic Chemistry, 1983, vol. 48, # 18, p. 2953 - 2956
[3] Tetrahedron Letters, 2013, vol. 54, # 44, p. 5849 - 5852
  • 4
  • [ 6704-31-0 ]
  • [ 7748-36-9 ]
YieldReaction ConditionsOperation in experiment
1 g With sodium tetrahydroborate In tetrahydrofuran at 25℃; for 4 h; To a suspension of oxetan-3-one (1.2 g) in THF (20 mL) was added NaBH4 (0.8 g). The resulting mixture was stirred at 25°C for 4 hours, and then quenched with aq. NH4CIsolution (10 mL). The resulting solution was dried with Na2SO4 overnight. After filtration, the solvent was removed under reduced pressure to afford oxetan-3-ol (1.0 g).
Reference: [1] Patent: WO2015/181186, 2015, A1, . Location in patent: Page/Page column 169
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 6, p. 2518 - 2532
  • 5
  • [ 24573-30-6 ]
  • [ 109-92-2 ]
  • [ 106-89-8 ]
  • [ 7748-36-9 ]
Reference: [1] Patent: US6140271, 2000, A,
  • 6
  • [ 24573-30-6 ]
  • [ 106-89-8 ]
  • [ 7748-36-9 ]
Reference: [1] Patent: US4395561, 1983, A,
  • 7
  • [ 85328-34-3 ]
  • [ 7748-36-9 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 2, p. 433 - 442
  • 8
  • [ 7748-36-9 ]
  • [ 98-59-9 ]
  • [ 26272-83-3 ]
YieldReaction ConditionsOperation in experiment
94% With triethylamine In water at 20℃; for 18 h; Scheme 613 Step 1 14 Step 2 15Step 1To a solution of 1.00 g (13.5 mmol) of compound 13 and 7.6 mL (54.0 mmol) of triethylamine in 27 mL of methylene chloride was added 5.15 g (27.0 mmol) of p- toluenesulfonyl chloride. The reaction mixture was stirred at room temperature overnight. After this time, the reaction was quenched with saturated 150 mL of aqueous sodium bicarbonate and extracted with three 50 mL portions of methylene chloride. The combined extracts were concentrated and the resulting residue was purified by column chromatography (silica, 0-25percent EtOAc/hexanes) to give 1.22 g (94percent) of 14 as white solid: NMR (CDCI3 500 MHz) δ 7.78 (d, J= 8.5 Hz, 2H), 7.36 (d, J= 9.0 Hz, 2H), 5.29 (m, 1H), 4.69 (m, 4H), 2.46 (s, 3H).
85% With sodium hydroxide In water at 0℃; for 3 h; At 0° C., aqueous NaOH solution (2 N, 15 mL) was added dropwise to a solution of oxetan-3-ol (1.48 g, 20 mmol) and p-toluene sulfonyl chloride (4.18 g, 22 mmol) in water (50 mL). After stirred for 3 hours, the mixture was treated with water (100 mL), extracted with dichloromethane (100 mL×3). The organic layers were combined, dried over anhydrous sodium sulfate, then filtrated, the filtrate was concentrated under reduced pressure. The residue was purified by silica column chromatography (petroleum ether:ethyl acetate=10:1) to give compound 39-c (3.9 g, yield: 85percent). LC-MS (ESI): m/z=229 [M+H]+.
78% at 20℃; Inert atmosphere ;To a 50 mL two-neck flask were added oxetan-3-ol (1.00 g, 13.0 mmol) and anhydrous pyridine (25 mL), then paratoluensulfonyl chloride (3.10 g, 16.0 mmol) was added to the mixture under nitrogen protection.
The reaction mixture was stirred at rt overnight.
The reaction was mornitored by TLC until oxetan-3-ol consumed completely, then the mixture was concentrated in vacuo to remove pyridine.
To the residue was added saturated brine (60 mL).
The resulting mixture was extracted with EtOAc (20 mL*3).
The combined organic layers were washed with saturated brine (30 mL*2), dried over anhydrous Na2SO4, and filtered.
The filtrate was concentrated in vacuo, and the residue was purified by silica-gel column chromatography (PE:EtOAc=10:1, V/V) to give a white solid (2.40 g, 78.0percent).
MS(ESI, pos.ion)m/z:229.1 (M+1);
65% With sodium hydroxide In water at 50℃; for 1 h; To a well-stirred 50° C. solution of Part D compound (7 g, 94 mmol) and p-TsCl (12.8 g, 67.1 mmol) in water (15 mL) was added dropwise a solution of NaOH (2.69 g, 67.1 mmol) in water (15 mL). The reaction was heated for 1 h at 50° C., then cooled to RT and toluene (10 mL) was added. The aqueous layer was extracted with toluene (5 mL.x.2). The combined organic extracts were washed with conc NH4OH (3.x.) and water (2.x.), then concentrated in vacuo. Hexane (50 mL) was added to the residue and a solid was formed, which was collected by filtration and then was dried in vacuo for 1 h to give Part E compound (10 g, 65percent yield) as a white solid. [M+H]+=229.1; 1H NMR (400 MHz, CDCl3) δ ppm 2.46 (s, 3 H), 4.64-4.75 (m, 4 H), 5.27-5.34 (m, 1 H), 7.37 (d, J=8.25 Hz, 2 H), 7.78 (d, J=8.25 Hz, 2 H).
62% at 20℃; for 18 h; Preparation of toluene-4-sulfonic acid oxetan-3-yl ester; To a solution of oxetan-3-ol (1.0 g, 13.0 mmol) in anhydrous pyridine (25 ml_) at room temperature was added 4-toluene sulfonyl chloride (3.09 g, 16.2 mmol). After stirring the reaction mixture for 18 hours at room temperature, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by flash chromatography over silica gel eluting with a gradient of 0 to 30percent ethyl acetate in heptane to afford 1.9 g (62percent yield) of the desired product as a white solid.1H NMR (400 MHz, chloroform-d) delta ppm 2.46 (s, 3 H), 4.63 - 4.75 (m, 4 H), 5.26 - 5.34 (m, 1 H), 7.36 (d, J=8.00 Hz, 2 H), 7.78 (d, J=8.40 Hz, 2 H).
50% With triethylamine In dichloromethane at 20℃; for 15 h; Step 1: To a stirred mixture of oxetan-3-ol (0.85 g, 11.5 mmol) in DCM (38 mL) were added TEA (3.3 mL, 23mmol) and 4-methylbenzene-1-sulfonyl chloride (2.7 g, 13.8 mmol). The reaction mixture was stirred at rt for 15 h. Themixture was partitioned between water and DCM. The organic layer was separated, dried over Na2SO4, filtered, andconcentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with a gradientof 30percent DCM in petroleum ether to 100percent DCM to afford oxetan-3-yl 4-methylbenzenesulfonate (1.3 g, 50percent) as a whitesolid. 1H NMR (300 MHz, CDCl3) δ 7.77 (d, J = 8.4 Hz, 2H), 7.35 (d, J = 8.7 Hz, 2H), 5.30 (m, 1H), 4.66 - 4.74 (m, 4H),2.46 (s, 3H); LCMS (ESI) m/z 229 (M+H)+

Reference: [1] Patent: WO2012/138678, 2012, A1, . Location in patent: Page/Page column 33
[2] Journal of Organic Chemistry, 1983, vol. 48, # 18, p. 2953 - 2956
[3] Patent: US2015/336982, 2015, A1, . Location in patent: Paragraph 0290; 0291
[4] Patent: EP3342765, 2018, A1, . Location in patent: Paragraph 0293
[5] Patent: US2008/9465, 2008, A1, . Location in patent: Page/Page column 82
[6] Organic Letters, 2008, vol. 10, # 15, p. 3259 - 3262
[7] Patent: WO2010/23594, 2010, A1, . Location in patent: Page/Page column 34
[8] Patent: EP2766359, 2016, B1, . Location in patent: Paragraph 0974
[9] Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 2, p. 433 - 442
[10] Patent: US2007/66620, 2007, A1, . Location in patent: Page/Page column 14
  • 9
  • [ 7748-36-9 ]
  • [ 124-63-0 ]
  • [ 148430-81-3 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane at 0 - 20℃; for 3 h; To a solution of oxetan-3-ol (5 g, 67.5 mmol) and triethylamine (14.11 mL, 101 mmol) in DCM (150 mL) at 0°C was added methanesulfonyl chloride (6.79 mL, 88 mmol) dropwise. The mixture was stirred at RT for 3 hr. The solid was filtered off and the filtrate was washed with ice -water and brine solution. The organic phase was dried over anhydrous Na2S04 and concentrated in vacuo to afford the title compound (11.7 g, 67.5 mmol, 100percent yield) as an oil (containing 12.2 wtpercent of DCM). lU NMR (400 MHz, CDC13) δ 3.06 (s, 3H), 4.79-4.82 (m, 2H), 4.86-4.90 (m, 2H), 5.52-5.49 (m, 1H).
75.7%
Stage #1: With triethylamine In dichloromethane at 0℃; for 0.333333 h;
Stage #2: at 20℃; for 12 h;
The oxetan-3-ol 16a (10.0 g, 135.0 mmol) was dissolved in dichloromethane (300 mL) at room temperature,After cooling to 0 ° C, triethylamine (20.4 g, 202.0 mmol) was added and stirred for 20 minutes.Methylsulfonyl chloride (20.08 g, 176.0 mmol) was added dropwise to the reaction solution and allowed to react at room temperature for 12 hours.The reaction solution was filtered and the filter cake was washed with dichloromethane (100 mL x 2), the organic phases were combined,Washed successively with water (200 mL x 1), saturated brine aqueous solution (200 mL x 1).Dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give pale yellow solid 16b (15.6 g, yield 75.7percent).
1.2 g With triethylamine In dichloromethane at 20℃; for 2 h; Cooling with ice To an ice-water cooled solution of oxetan-3-ol (1.0 g) in DCM (50 mL) was added TEA (3.8 mL). MsCI (1 .6 mL) was then added dropwise. The resulting mixture was warmed up slowly and stirred at RT for 2 hours. The mixture was then quenched with aq. NaHCO3 solutionand extracted with EA (3x50 mL). The combined organic phases were washed, dried and concentrated to afford oxetan-3-yl methanesulfonate (1.2 g).
Reference: [1] Patent: WO2013/55910, 2013, A1, . Location in patent: Page/Page column 124; 125
[2] Patent: TW2017/8221, 2017, A, . Location in patent: Page/Page column 98; 99
[3] Patent: WO2015/181186, 2015, A1, . Location in patent: Page/Page column 169
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 23, p. 9769 - 9789
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 6, p. 2518 - 2532
  • 10
  • [ 7748-36-9 ]
  • [ 1339890-99-1 ]
Reference: [1] Patent: US2014/323481, 2014, A1, . Location in patent: Paragraph 0396-0397
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